CA2034762A1 - Process for preparation of condensed alcohols by alkoxide catalysis - Google Patents
Process for preparation of condensed alcohols by alkoxide catalysisInfo
- Publication number
- CA2034762A1 CA2034762A1 CA002034762A CA2034762A CA2034762A1 CA 2034762 A1 CA2034762 A1 CA 2034762A1 CA 002034762 A CA002034762 A CA 002034762A CA 2034762 A CA2034762 A CA 2034762A CA 2034762 A1 CA2034762 A1 CA 2034762A1
- Authority
- CA
- Canada
- Prior art keywords
- alcohol
- aldehyde
- alkoxide
- alcohols
- dimer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 31
- 150000004703 alkoxides Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 26
- 238000006555 catalytic reaction Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000539 dimer Substances 0.000 claims abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- -1 potassium alkoxide Chemical class 0.000 claims description 21
- 150000003138 primary alcohols Chemical class 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 8
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 238000007037 hydroformylation reaction Methods 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 18
- 229910052723 transition metal Inorganic materials 0.000 abstract description 5
- 150000003624 transition metals Chemical class 0.000 abstract description 5
- 150000001299 aldehydes Chemical class 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 8
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 5
- 239000004440 Isodecyl alcohol Substances 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000004808 allyl alcohols Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 229910000570 Cupronickel Inorganic materials 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
- C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476,163 | 1990-02-01 | ||
| US07/476,163 US5068469A (en) | 1990-02-07 | 1990-02-07 | Process for preparation of condensed alcohols by alkoxide catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2034762A1 true CA2034762A1 (en) | 1991-08-02 |
Family
ID=23890751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002034762A Abandoned CA2034762A1 (en) | 1990-02-01 | 1991-01-22 | Process for preparation of condensed alcohols by alkoxide catalysis |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5068469A (zh) |
| EP (1) | EP0440420B1 (zh) |
| JP (1) | JPH0517381A (zh) |
| KR (1) | KR910021357A (zh) |
| CN (1) | CN1028095C (zh) |
| AT (1) | ATE161816T1 (zh) |
| AU (1) | AU632202B2 (zh) |
| BR (1) | BR9100409A (zh) |
| CA (1) | CA2034762A1 (zh) |
| DE (1) | DE69128547D1 (zh) |
| MY (1) | MY105346A (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210351A (en) * | 1986-09-19 | 1993-05-11 | Pennzoil Products Company | Preparation of alkylated cyclopentadienes |
| DE10046433A1 (de) * | 2000-09-20 | 2002-04-04 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Guerbetalkoholen |
| CN103119013B (zh) | 2010-09-15 | 2015-06-17 | 三仪股份有限公司 | 通过格尔伯特反应制造醇的方法 |
| US8809594B2 (en) | 2012-09-21 | 2014-08-19 | Eastman Chemical Company | Dual catalyst system for the self-condensation of alcohols |
| CN104689857B (zh) * | 2015-03-26 | 2018-10-19 | 中国科学院青岛生物能源与过程研究所 | 氮掺杂多孔碳材料的制备方法以及含该材料的催化剂及用途 |
| US9828322B2 (en) | 2016-01-28 | 2017-11-28 | Eastman Chemical Company | Efficient synthesis of methacroelin and other alpha, beta-unsaturated aldehydes over a regenerable anatase titania catalyst |
| US9834501B2 (en) | 2016-01-28 | 2017-12-05 | Eastman Chemical Company | Efficient synthesis of methacroelin and other alpha, beta—unsaturated aldehydes from methanol and an aldehyde |
| BR102019024934B1 (pt) | 2019-11-26 | 2022-02-22 | Petróleo Brasileiro S.A. - Petrobras | Processo para obtenção de compostos, dentre os quais o triptano por reação de acoplamento de álcoois |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1992480A (en) * | 1930-07-26 | 1935-02-26 | Degussa | Process for the production of higher alcohols, particularly butyl alcohol, from ethyl alcohol |
| US2457866A (en) * | 1945-05-26 | 1949-01-04 | Carbide & Carbon Chem Corp | Condensation of alcohols |
| US2762847A (en) * | 1953-05-05 | 1956-09-11 | Monsanto Chemicals | Manufacture of alcohols by guerbet condensation |
| US2836628A (en) * | 1955-10-17 | 1958-05-27 | Monsanto Chemicals | Unsaturated branched-chain alcohols and methods of preparing same |
| US2862013A (en) * | 1955-11-16 | 1958-11-25 | Monsanto Chemicals | Branched-chain higher alcohols formed by condensation of lower alcohols, and esters of said higher alcohols |
| US3119880A (en) * | 1961-05-29 | 1964-01-28 | Gulf Research Development Co | Condensation of alcohols |
| US3328470A (en) * | 1963-10-03 | 1967-06-27 | Continental Oil Co | Greater selectivity in the guerbet reaction |
| DE1223822B (de) * | 1965-01-27 | 1966-09-01 | Deutsche Erdoel Ag | Verfahren zur Herstellung von beta-verzweigten, gesaettigten und ungesaettigten Aldehyden |
| NL6706692A (zh) * | 1966-05-18 | 1967-11-20 | ||
| NL6709801A (zh) * | 1966-07-21 | 1968-01-22 | ||
| US3544635A (en) * | 1968-04-15 | 1970-12-01 | Ethyl Corp | Process for preparing alcohols and aldehydes |
| US3916015A (en) * | 1973-04-11 | 1975-10-28 | Continental Oil Co | Process for condensation of alcohols |
| US3860664A (en) * | 1973-06-06 | 1975-01-14 | Continental Oil Co | Process for condensation of alcohols |
| JPS58159432A (ja) * | 1982-03-18 | 1983-09-21 | Kao Corp | 分枝二量化アルコ−ルの製造方法 |
| US4590314A (en) * | 1983-12-30 | 1986-05-20 | Union Carbide Corporation | Catalytic process for the production of alcohols from carbon monoxide, hydrogen and olefins |
| US4681868A (en) * | 1986-05-29 | 1987-07-21 | The Standard Oil Company | Oxygenate condensation catalyst |
-
1990
- 1990-02-07 US US07/476,163 patent/US5068469A/en not_active Expired - Fee Related
-
1991
- 1991-01-19 MY MYPI91000090A patent/MY105346A/en unknown
- 1991-01-22 CA CA002034762A patent/CA2034762A1/en not_active Abandoned
- 1991-01-29 DE DE69128547T patent/DE69128547D1/de not_active Expired - Lifetime
- 1991-01-29 AT AT91300669T patent/ATE161816T1/de not_active IP Right Cessation
- 1991-01-29 EP EP91300669A patent/EP0440420B1/en not_active Expired - Lifetime
- 1991-01-30 JP JP9127673A patent/JPH0517381A/ja active Pending
- 1991-01-31 KR KR1019910001672A patent/KR910021357A/ko not_active Application Discontinuation
- 1991-01-31 BR BR919100409A patent/BR9100409A/pt not_active Application Discontinuation
- 1991-01-31 CN CN91100562A patent/CN1028095C/zh not_active Expired - Fee Related
- 1991-01-31 AU AU70105/91A patent/AU632202B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN1054583A (zh) | 1991-09-18 |
| BR9100409A (pt) | 1991-10-22 |
| DE69128547D1 (de) | 1998-02-12 |
| KR910021357A (ko) | 1991-12-20 |
| CN1028095C (zh) | 1995-04-05 |
| US5068469A (en) | 1991-11-26 |
| AU7010591A (en) | 1991-08-08 |
| EP0440420B1 (en) | 1998-01-07 |
| AU632202B2 (en) | 1992-12-17 |
| ATE161816T1 (de) | 1998-01-15 |
| JPH0517381A (ja) | 1993-01-26 |
| EP0440420A1 (en) | 1991-08-07 |
| MY105346A (en) | 1994-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |